Substituted arylazadioxacyclo alkene fungicides

Abstract

The invention relates to novel substituted arylazadioxacycloalkenes, a plurality of processes for their preparation and to their use as fungicides.

Claims

1. Compounds of the formula (I) ##STR91## in which A represents optionally substituted alkylene.

Ar.sup.1, Ar.sup.2 independently of one another each represent optionally substituted arylene or heteroarylene.

E represents a 1-alkene-1,1-diyl grouping which contains a radical R.sup.1 in position 2, or represents a 2-aza-1-alkene-1,1-diyl grouping which contains a radical R.sup.2 in position 2, or represents an optionally substituted imino grouping N--R.sup.3, or represents a 3-aza-1-propene-2,3-diyl grouping which contains a radical R.sup.4 in position 1 and a radical R.sup.5 in position 3, or represents a 3-aza-1-propene-2,3-diyl grouping which contains a radical R.sup.4 in position 1, or represents a 3-thia-1-propene-2,3-diyl grouping which contains a radical R.sup.4 in position 1, or represents a 1-aza-1-propene-2,3-diyl grouping which contains a radical R.sup.6 in position 1 and a radical R.sup.5 in position 3, or represents a 1-aza-1-propene-2,3-diyl grouping which contains a radical R.sup.4 in position 1 and a radical R.sup.5 in position 3, or represents a 1,3-diaza-1-propene -2,3-diyl grouping which contains a radical R.sup.6 in position 1 and a radical R.sup.5 in position 3, or represents a 1-aza-3-oxa-1-propene-2,3-diyl grouping which contains a radical R.sup.6 in position 1, or represents a 1-aza-3-thia-1-propene-2,3-diyl grouping which contains a radical R.sup.6 in position 1, wherein

R.sup.1, R.sup.4 each represent hydrogen, halogen, cyano or represent optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,

R.sup.2, R.sup.6 each represent hydrogen, amino, cyano or represent optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and

R.sup.3 represents hydrogen, cyano or represents optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkylalkyl,

R.sup.5 represents alkyl,

G represents a single bond, represents oxygen, sulphur, or represents optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or cycloalkyl-substituted alkanediyl, alkenediyl, alkinediyl or represents a substitustent selected from the group of consisting of

--Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--; --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 --, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, --N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n --, --CQ--, --S(O).sub.n --CH.sub.2 --, --C(R.sup.7).dbd.N--O--, --C(R.sup.7)----N--O--CH.sub.2 --, --N(R.sup.8)--, --CQ--N(R.sup.8)--, --N(R.sup.8)--CQ--, --Q--CQ--N(R.sup.8)--, --N.dbd.C(R.sup.7)--Q--CH.sub.2 --, --CH.sub.2 --O--N.dbd.C(R.sup.7)--, --N(R.sup.8)--CQ--Q--, --CQ--N(R.sup.8)--CQ--Q--, --N(R.sup.8)--CQ--Q--CH.sub.2 --,--Q--C(R.sup.7).dbd.N--O--CH.sub.2 --, --N(R.sup.8)--C(R.sup.7).dbd.N--O--CH.sub.2 --, O--CH.sub.2 --C(R.sup.7).dbd.N--O--, --N.dbd.N--C(R.sup.7)--N--O--, --T--Ar.sup.3 --and --T--Ar.sup.3 --Q--, wherein

Ar.sup.3 represents optionally substituted arylene, heteroarylene, cycloalkylene or heterocycloalkylene,

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulphur,

R.sup.7 represents hydrogen, cyano or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and

R.sup.8 represents hydrogen, hydroxyl, cyano or respectively optionallysubstituted alkyl, alkoxy or cycloalkyl and

T represents a single bond, represents oxygen, sulphur, --CH.sub.2 --O--, CH.sub.2 --S-- or represents optionally substituted alkanediyl and

R represents alkyl, alkoxy, hydroxylamino, alkoxamino, alkylamino or dialkylamino.

2. Compounds of the formula (I) according to claim 1 in which

A represents alkylene having 1 to 4 carbon atoms,

Ar.sup.1 represents respectively optionally substituted phenylene or naphthylene,represents mono- or dicyclic heteroarylene having in each case 5 or 6 ring members or represents benzo-fused heteroarylene having 5 or 6 ring members, at least one of which in each case is oxygen, sulphur or nitrogen and one or two more of which optionally are nitrogen, wherein the substituents are selected from the group consisting of

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, represents straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms, represents straight-chain or branched alkenyl, alkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, represents straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkyl sulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, represents straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, represents straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, alkylene or dioxyalkylene, each of which has 1 to 6 carbon atoms, is attached twice and is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,

Ar.sup.2 represents phenylene or naphthylene or represents heteroarylene having 3 to 7 ring members, each of the radicals being optionally mono- or polysubstituted by identical or different substituents and at least one of the 3 to 7 ring members being oxygen, sulphur or nitrogen and one or two more optionally being nitrogen, wherein the substitutents are selected from the group consisting of

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl,thiocarbamoyl;

represents straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;

represents straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;

represents straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;

respectively straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;

respectively straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;

alkylene or dioxyalkylene, each of which has 1 to 6 carbon atoms, is attached twice and is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;

cycloalkyl having 3 to 6 carbon atoms;

E represents one of the groupings below: ##STR92## in which R.sup.1 represents hydrogen, halogen, cyano or represents optionally halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, alkoxy, alkylthio,alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl radicals,

R.sup.2 represents hydrogen, amino, cyano or represents optionally halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, alkoxy, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl radicals,

R.sup.3 represents hydrogen, cyano or represents optionally halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, alkenyl or alkinyl having in each case up to 6 carbon atoms or represents optionally halogen-, cyano-, carboxyl-, C.sub.1 -C.sub.4 -alkyl- or C.sub.1 -C.sub.4 -alkoxy-carbonyl-substituted cycloalkyl or cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moieties and optionally 1 to 4 carbon atoms in the alkyl moiety,

R.sup.4 represents hydrogen, halogen, cyano or represents optionally halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, alkoxy, alkylthio,alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl radicals,

R.sup.5 represents alkyl having 1 to 6 carbon atoms and

R.sup.6 represents hydrogen, amino, cyano or represents optionally halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, alkoxy, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl radicals;

G represents a single bond, represents oxygen, sulphur or represents respectively optionally halogen-, hydroxyl-, C.sub.1 -C.sub.4 -alkyl-, C.sub.1 -C.sub.4 -halogenoalkyl- or C.sub.3 -C.sub.6 -cycloalkyl-substituted alkanediyl, alkenediyl, alkinediyl having in each case up to 4 carbon atoms or represents a substiuent selected from the group consisting of

--Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--; --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 --, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, --N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n,--, --CQ--, --S(O)n--CH.sub.2 --, --C(R.sup.7).dbd.N--O--, --C(R7).dbd.N--O--CH.sub.2 --, --N(R.sup.8)--, --CQ--N(R.sup.8)--, --N(R.sup.8)--CQ--, --Q--CQ--N(R.sup.8)--, --N.dbd.C(R.sup.7)--Q--CH.sub.2 --, --CH.sub.2 --O--N.dbd.C(R.sup.7)--, --N(R.sup.8)--CQ--Q--, --CQ--N(R.sup.8)--CQ--Q--, --N(R.sup.8)--CQ--Q--CH.sub.2 --, --Q--C(R.sup.7).dbd.N--O--CH.sub.2 --, --N(R.sup.8)--C(R.sup.7).dbd.N--O--CH.sub.2 --, --O--CH.sub.2 --C(R.sup.7).dbd.N--O--, --N.dbd.N--C(R.sup.7).dbd.N--O--, --T--Ar.sup.3 and --T--A.sup.3 --Q--, wherein

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulphur,

R.sup.7 represents hydrogen, cyano, represents optionally halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, or represents optionally halogen-, cyano-, carboxyl-, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, and

R.sup.8 represents hydrogen, hydroxyl, cyano or represents optionally halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms, or represents optionally halogen-, cyano-, carboxyl-, C.sub.1 -C.sub.4 -alkyl- or C1-C4-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms and

Ar.sup.3 represents phenylene, naphthylene, cycloalkylene or representsheteroarylene or heterocycloalkylene having 3 to 7 ring members, each of the radicals being optionally mono- or polysubstituted by identical or different substituents and at least one of the 3 to 7 ring members being oxygen, sulphur or nitrogen and one or two more optionally being nitrogen, wherein the substituents are selected from the group consisting of

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, and thiocarbamoyl

represents straight-chain or branched alkyl, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;

represents straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;

represents straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;

represents straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;

respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and;

cycloalkyl having 3 to 6 carbon atoms and

T represents a single bond, represents oxygen, sulphur --CH.sub.2 --O--, CH.sub.2 --S-- or represents alkanediyl having 1 to 3 carbon atoms,

R represents alkyl, alkoxy, alkylamino, hydroxylamino, alkoxyamino ordialkylamino having in each case 1 to 4 carbon atoms.

3. Compounds of the formula (I) according to claim 1 in which

A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or 1,3-i-butylene,

Ar.sup.1 represents optionally substituted ortho-, meta- or paraphenylene, represents furanediyl, thiophenediyl, pyrrolediyl,pyrazolediyl, triazolediyl, oxazolediyl, isoxazolediyl, thiazolediyl, isothiazolediyl, oxadiazolediyl, thiadiazolediyl, pyridinediyl (in particular pyridine-2,3-diyl), pyrimidinediyl, pyridazinediyl, pyrazinediyl, 1,3,4-triazinediyl or 1,2,3-triazinediyl, wherein the substituents areselected from the group consisting of

fluorine, chlorine, cyano, methyl, ethyl, cyclopropyl, trifluoromethyl, methoxy, ethoxy, methylthio, methylsulphinyl and methylsulphonyl,

Ar.sup.2 represents phenylene, naphthylene, furanediyl, thiophenediyl, oxazolediyl, isoxazolediyl, thiazolediyl, isothiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl, 1,2,4-thiadiazolediyl, 1,3,4-thiadiazolediyl, pyridinediyl, pyrimidinediyl, pyridazinediyl, pyrazinediyl, I,2,3-triazinediyl, 1,2,4-triazinediyl, 1,3,5-triazinediyl, each of which is optionally mono- to trisubstituted by identical or different substituents, wherein the substituents are selected from the groupconsisting of

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methy Isulphony loxy, ethylsulphonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl and ethoximinoethyl;

E represents a substituent selected from the group consisting of ##STR93## in which R.sup.1 represents hydrogen, fluorine, chlorine, bromine, cyano or represents optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, propyl, methoxy, ethoxy, methylthio, ethylthio,methylamino, ethylamino or dimethylamino,

R.sup.2 represents hydrogen, amino, cyano or represents optionallyfluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino,

R.sup.3 represents hydrogen, cyano or represents optionally fluorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, represents allyl or propargyl or represents respectively optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, ethyl-, n- or i-propyl-, methoxy-carbonyl- or ethoxy-carbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,

R.sup.4 represents hydrogen, fluorine, chlorine, bromine, cyano or represents optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,

R.sup.5 represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,

R.sup.6 represents hydrogen, amino, cyano or represents optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino, and

G represents a single bond, represents oxygen, sulphur, or represents respectively optionally fluorine-, chlorine-, bromine-, hydroxyl-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, cyclopropyl-, cyclobutyl-, cyclopentyl- or cyclohexyl-substituted methylene, dimethylene (ethane-1,2-diyl), ethene-1,2-diyl, ethine-1,2-diyl or represents a substituent selected from the group consisting of

--Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--; --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 --, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, --N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n --, --CQ--, --S(O).sub.n --CH.sub.2 --, --C(R.sup.7).dbd.N--O--, --C(R7).dbd.N--O--CH.sub.2 --, --N(R.sup.8)--, --CQ--N(R.sup.8)--, --N(R.sup.8)--CQ--, --Q--CQ--N(R.sup.8)--, --N.dbd.C(R.sup.7)--Q--CH.sub.2 --, --CH.sub.2 --O--N.dbd.C(R.sup.7)--, --N(R.sup.8)--CQ--Q--, --CQ--N(R.sup.8)--CQ--Q--, --N(R.sup.8)--CQ--Q--CH.sub.2 --, --Q--C(R.sup.7)----N--O--CH.sub.2 --, --N(R.sup.8)--C(R.sup.7).dbd.N--O--CH.sub.2 --, --O--CH.sub.2 --C(R.sup.7).dbd.N--O--, --N.dbd.N--C(R.sup.7).dbd.N--O--, --T--Ar.sup.3 and --T--Ar.sup.3 --Q--, wherein

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulphur,

R.sup.7 represents hydrogen, cyano, represents optionally fluorine-, chlorine-, cyano-, methoxy- or etlioxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, propoxy, butoxy, methylthio, ethylthio, propylthio, butylthio, methylamino, ethylamino, propylamino, dimethylamino or diethylamino or represents optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, ethyl-, n- or i-propyl-, methoxycarbonyl- or ethoxy-carbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and

R.sup.8 represents hydrogen, hydroxyl, cyano or represents optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or. represents optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, ethyl-, n- or i-propyl-, methoxy-carbonyl- or ethoxy-carbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl cyclohexyl,

Ar.sup.3 represents phenylene, naphthylene, furanediyl, thiophenediyl, oxazolediyl, isoxazolediyl, thiazolediyl, isothiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl, 1,2,4-thiadiazolediyl, 1,3,4-thiadiazolediyl, pyridinediyl, pyrimidinediyl, pyridazinediyl, pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl, 1,3,5-triazinediyl, oxiranediyl, oxetanediyl, tetrahydrofuranediyl, perhydropyranediyl or pyrrolidinediyl, each of which is optionally mono- to trisubstituted, wherein the substituents are selected from the groud consisting of

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl,, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl and cyclopropyl and

T represents a single bond, represents oxygen, sulphur, --CH.sub.2 --O--, CH.sub.2 --S--, methylene, ethylene or propylene and

R represents methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino, hydroxylamino, methoxyamino, dimethylamino, diethylamino.

4. Compounds of the formula (1) according to claim 1

A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene,

Ar.sup.1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,

Ar.sup.2 represents phenylene which is optionally mono- to trisubstituted by identical or different substituents, wherein the substituents are selected from the group consisting of

fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluomethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl,

methylenedioxy and ethylenedioxy, each of which is attached twice and each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl,

E represents a substituent selected from the group consisting of ##STR94## in which R.sup.1 and R.sup.2 each represent methoxy and

R.sup.3 represents hydrogen, cyano, methyl, ethyl, n- or i-propyl, methoxy or ethoxy,

G represents oxygen or represents optionally fluorine-, chlorine- or bromine-substituted dimethylene (ethane-1,2-diyl), ethene-1,2-diyl or represents a substituent selected from the group consisting of

--Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--; --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 --, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, --N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n --, --CQ--, --S(O).sub.n --CH.sub.2 --, --C(R.sup.7).dbd.N--O--, --C(R7).dbd.N--O--CH.sub.2 --, --N(R.sup.8)--, --CQ--N(R.sup.8)--, --N(R.sup.8)--CQ--, --Q--CQ--N(R.sup.8)--, --N.dbd.C(R.sup.7)--Q--CH.sub.2 --, --CH.sub.2 --O--N.dbd.C(R.sup.7)--, --N(R.sup.8)--CQ--Q--, --CQ--N(R.sup.8)--CQ--Q--, --N(R.sup.8)--CQ--Q--CH.sub.2 --, --Q--C(R.sup.7).dbd.N--O--CH.sub.2 --, --N(R.sup.8)--C(R.sup.7).dbd.N--O--CH.sub.2 --, --O--CH.sub.2 --C(R.sup.7).dbd.N--O--, --N.dbd.N--C(R.sup.7).dbd.N--O--, --T--Ar.sup.3 and --T--Ar.sup.3 --Q--, wherein

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulphur,

R.sup.7 represents hydrogen, cyano, methyl, ethyl or cyclopropyl and

R.sup.8 represents hydrogen, methyl, ethyl or cyclopropyl,

Ar.sup.3 represents phenylene, 1,2,4-thiadiazolediyl, 1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl, pyridinediyl, pyrimidinediyl, pyridazinediyl pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl or 1,3,5-triazinediyl, each of which is optionally mono- to trisubstituted by identical or different substituents, wherein the substituents are selected from the group consisting of

fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl and trifluoromethylsulphonyl, and

T represents a single bond, represents oxygen, sulphur, --CH.sub.2 --O--, CH.sub.2 --S--, methylene, ethylene or propylene and

R represents methyl, ethyl, methoxy, methylamino or hydroxylamino.

5. Compounds of the formula (I) according to claim 1

A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene,

Ar.sup.1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,

Ar.sup.2 represents phenylene which is in each case optionally mono- to trisubstituted by identical or different substituents, wherein the substituents are selected from the group consisting of fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluomethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl,

methylenedioxy and ethylenedioxy, each of which is attached twice and each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl or ethyl,

E represents ##STR95## in which R.sup.1 and R.sup.2 each represent methoxy and

G represents --O--CH.sub.2 and

R represents methyl, ethyl, methoxy, methylamino or hydroxylamino.

6. Compounds of the formula (1) according to claim 1

A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene,

Ar.sup.1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,

Ar.sup.2 represents phenylene which is optionally mono- to trisubstituted by identical or different substituent selected from the group consisting of

fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluomethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximino ethyl, ethoximinoethyl,

methylenedioxy and ethylenedioxy, each of which is attached twice and each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl,

E represents ##STR96## in which R.sup.1 and R.sup.2 each represent methoxy and

G represents --C(R7).dbd.N--O--CH.sub.2 -- wherein

R.sup.7 represents hydrogen, cyano, methyl, ethyl or cyclopropyl and

R represents methyl, ethyl, methoxy, methyla mino or hydroxylamino.

7. Compounds of the formula (1) according to claim 1 in which

A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene,

Ar.sup.1 represents ortho-phenylene,

Ar.sup.2 represents phenylene which is optionally mono- to trisubstituted by identical or different substituents, wherein the substituents are selected from the group consisting of

fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluomethoxy, difluorochloromethoxy, trifluoroethoxy, difluomethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl,

methylenedioxy and ethylenedioxy, each of which is attached twice and each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl,

E represents ##STR97## in which R.sup.1 and R.sup.2 each represent methoxy,

G represents --T--Ar.sup.3 --Q-- wherein

Q represents oxygen or sulphur,

Ar.sup.3 represents 1,2,4-thiadiazolediyl, 1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl or represents pyridinediyl, pyrimidinediyl or 1,3,5-triazinediyl, each of which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine cyano, methyl, cyclopropyl, methoxy, methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, and difluorochlioromethoxy,

T represents a single bond, represents oxygen, sulphur, --CH.sub.2 --O--, CH.sub.2 --S--, methylene, ethylene or propylene and

R represents methyl, ethyl, methoxy, methylamino or hydroxylamino.

8. An insecticidal composition comprising an insecticidally effective amount of according to claim 1 and an extender.

9. A method of combatting insects which comprises administering to such a locus from which it is desired to exclude such insects an insecticidally unt of a compound according to claim 1.

10. Process for preparing compounds of the formula (I) according to claim 1, comprising reacting

a) hydroxyl compounds of the formula (II) ##STR98## in which A and Ar.sup.2 are each as defined in claim 1, with halogen compounds of the formula (III) ##STR99## in which G.sup.2 represents --Ar--Q-- or represents --Ar--,

Ar.sup.1, Ar.sup.3, E, Q and R are each as defined in claim 1 and

X represents halogen, optionally in the presence of an acid acceptor and optionally in the presence of a diluent;

b) reacting hydroxyl compounds of the formula (II) ##STR100## in which A and Ar.sup.2 are each as defined in claim 1, with halogen compounds of formula (IV) ##STR101## in which Ar.sup.1, E and R are each as defined in claim 1 and

X represents halogen, optionally in the presence of an acid acceptor and optionally in the presence of a diluent;

c) reacting esters of the formula (I-1) ##STR102## in which A, Ar.sup.1, Ar.sup.2, E and G are each as defined in claim 1 and

A.sup.1 represents alkyl, with amines of the formula (V), ##STR103## in which A.sup.2 and A.sup.3 independently of one another are each hydrogen, respectively optionally substituted alkyl, alkoxy or hydroxyl,

or an acid addition complex thereof optionally in the presence of an acid acceptor and optionally in the presence of a diluent.